An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide.

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Walker JR, Alshafie G, Abou-Issa H, Curley RW Jr

An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide.

Bioorg Med Chem Lett. 2002 Sep 2;12(17):2447-50.

PubMed ID
12161154 [ View in PubMed
]
Abstract

Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
TretinoinRetinoic acid receptor RXR-alphaKi (nM)0.4N/AN/ADetails
TretinoinRetinoic acid receptor RXR-betaKi (nM)0.5N/AN/ADetails
TretinoinRetinoic acid receptor RXR-gammaKi (nM)1.4N/AN/ADetails